CN1332738A - 3－(杂环基)－取代的苯甲酰基吡唑 - Google Patents

3－(杂环基)－取代的苯甲酰基吡唑 Download PDF

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Publication number: CN1332738A
Authority: CN; China
Prior art keywords: alkyl; base; methyl; nch; formula
Prior art date: 1998-12-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

CN99815254A

Other languages

English (en)

Chinese (zh)

Inventor

U·奈德雷恩

N·高茨

E·鲍曼

W·冯迪恩

S·库迪斯

K·兰格曼

G·梅尔

U·米斯利茨

M·维特夏尔

M·奥顿

K-O·维斯特法伦

H·沃尔特

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-12-04

Filing date

1999-12-02

Publication date

2002-01-23

1999-12-02 Application filed by BASF SE filed Critical BASF SE

2002-01-23 Publication of CN1332738A publication Critical patent/CN1332738A/zh

Status Pending legal-status Critical Current

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UYMQWGLCXYHTES-UHFFFAOYSA-N phenyl(1h-pyrazol-5-yl)methanone Chemical class C=1C=CC=CC=1C(=O)C1=CC=NN1 UYMQWGLCXYHTES-UHFFFAOYSA-N 0.000 title claims abstract description 33
125000000623 heterocyclic group Chemical group 0.000 title abstract 2
-1 phenylsulfonyloxy Chemical group 0.000 claims abstract description 161
150000001875 compounds Chemical class 0.000 claims abstract description 117
229910052760 oxygen Inorganic materials 0.000 claims abstract description 76
239000001257 hydrogen Substances 0.000 claims abstract description 37
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
239000000203 mixture Substances 0.000 claims abstract description 37
125000003545 alkoxy group Chemical group 0.000 claims abstract description 30
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 25
229910052736 halogen Inorganic materials 0.000 claims abstract description 20
238000002360 preparation method Methods 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 17
238000000034 method Methods 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 15
150000002431 hydrogen Chemical class 0.000 claims abstract description 13
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 10
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 9
239000002585 base Substances 0.000 claims description 266
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
239000003513 alkali Substances 0.000 claims description 15
GLGSZERYOLHNML-UHFFFAOYSA-N $l^{1}-oxidanyl(phenyl)methanone Chemical compound [O]C(=O)C1=CC=CC=C1 GLGSZERYOLHNML-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 14
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 13
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 8
238000006073 displacement reaction Methods 0.000 claims description 7
230000000269 nucleophilic effect Effects 0.000 claims description 7
150000003217 pyrazoles Chemical class 0.000 claims description 6
230000004913 activation Effects 0.000 claims description 5
239000011814 protection agent Substances 0.000 claims description 5
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims description 4
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
230000008635 plant growth Effects 0.000 claims description 3
VMSLCPKYRPDHLN-UHFFFAOYSA-N (R)-Humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
150000001555 benzenes Chemical class 0.000 claims 2
125000001475 halogen functional group Chemical group 0.000 claims 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 7
125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract description 3
125000001188 haloalkyl group Chemical group 0.000 abstract description 3
125000003302 alkenyloxy group Chemical group 0.000 abstract description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
230000008569 process Effects 0.000 abstract description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
125000004438 haloalkoxy group Chemical group 0.000 abstract 1
125000004441 haloalkylsulfonyl group Chemical group 0.000 abstract 1
125000004995 haloalkylthio group Chemical group 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 75
239000001301 oxygen Substances 0.000 description 73
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 72
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 49
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
229910052731 fluorine Inorganic materials 0.000 description 33
239000011737 fluorine Substances 0.000 description 33
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 28
229910052794 bromium Inorganic materials 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
241000196324 Embryophyta Species 0.000 description 23
229910052801 chlorine Inorganic materials 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
125000005843 halogen group Chemical group 0.000 description 16
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
239000002253 acid Substances 0.000 description 11
230000002363 herbicidal effect Effects 0.000 description 11
229910052740 iodine Inorganic materials 0.000 description 11
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
239000006185 dispersion Substances 0.000 description 9
239000011630 iodine Substances 0.000 description 9
NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
239000003921 oil Substances 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 7
238000012360 testing method Methods 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
125000006125 ethylsulfonyl group Chemical group 0.000 description 6
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
230000002349 favourable effect Effects 0.000 description 5
239000004009 herbicide Substances 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000003446 ligand Substances 0.000 description 5
235000015320 potassium carbonate Nutrition 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 4
241000335053 Beta vulgaris Species 0.000 description 4
240000006122 Chenopodium album Species 0.000 description 4
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244000058871 Echinochloa crus-galli Species 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
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125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
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VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 4
150000002940 palladium Chemical class 0.000 description 4
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 3
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 3
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QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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239000013543 active substance Substances 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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230000006378 damage Effects 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
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PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
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KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000011280 coal tar Substances 0.000 description 1
238000004891 communication Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
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230000001276 controlling effect Effects 0.000 description 1
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239000010949 copper Substances 0.000 description 1
238000006352 cycloaddition reaction Methods 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
229940062233 di-isopropylammonium Drugs 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
150000004891 diazines Chemical class 0.000 description 1
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
239000002283 diesel fuel Substances 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
FSRXIRGQJIHEFB-UHFFFAOYSA-N diphenylphosphane;ethane Chemical compound CC.C=1C=CC=CC=1PC1=CC=CC=C1 FSRXIRGQJIHEFB-UHFFFAOYSA-N 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
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238000001035 drying Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
238000012407 engineering method Methods 0.000 description 1
229940052303 ethers for general anesthesia Drugs 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
244000000004 fungal plant pathogen Species 0.000 description 1
KGZJRXKGJRJKCB-UHFFFAOYSA-N hanf Chemical compound C=1C=CC=CC=1CC(C(=O)NC(CCCNC(N)=N)C(=O)NC(CC=1C=CC(O)=CC=1)C(O)=O)NC(=O)C(CO)NC(=O)C(CC(N)=O)NC(=O)C(CS)NC(=O)CNC(=O)C(CC(C)C)NC(=O)CNC(=O)C(CO)NC(=O)C(CCC(N)=O)NC(=O)C(C)NC(=O)CNC(=O)C(C(C)CC)NC(=O)C(CCCNC(N)=N)NC(=O)C(CC(O)=O)NC(=O)C(CCSC)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)CNC(=O)C(NC(=O)C(CS)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CCCNC(N)=N)NC(=O)C(CCCNC(N)=N)NC(=O)C(CC(C)C)NC(=O)C(N)CO)CC1=CC=CC=C1 KGZJRXKGJRJKCB-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000004571 lime Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
210000001699 lower leg Anatomy 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 description 1
239000012875 nonionic emulsifier Substances 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
150000008048 phenylpyrazoles Chemical class 0.000 description 1
PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
229940061584 phosphoramidic acid Drugs 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
235000013526 red clover Nutrition 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000013517 stratification Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000019635 sulfation Effects 0.000 description 1
238000005670 sulfation reaction Methods 0.000 description 1
125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
125000005537 sulfoxonium group Chemical group 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000013589 supplement Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
229910001428 transition metal ion Inorganic materials 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
229940087291 tridecyl alcohol Drugs 0.000 description 1
WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
235000018322 upland cotton Nutrition 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CN99815254A 1998-12-04 1999-12-02 3－(杂环基)－取代的苯甲酰基吡唑 Pending CN1332738A (zh)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19855850		1998-12-04
DE19855850.3		1998-12-04
DE19936514.8		1999-08-06
DE19936514		1999-08-06

Publications (1)

Publication Number	Publication Date
CN1332738A true CN1332738A (zh)	2002-01-23

Family

ID=26050547

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN99815254A Pending CN1332738A (zh)	1998-12-04	1999-12-02	3－(杂环基)－取代的苯甲酰基吡唑

Country Status (18)

Country	Link
US (1)	US6831039B1 (ja)
EP (1)	EP1135388B1 (ja)
JP (1)	JP2002531562A (ja)
KR (1)	KR20010080670A (ja)
CN (1)	CN1332738A (ja)
AT (1)	ATE249456T1 (ja)
AU (1)	AU2094900A (ja)
BG (1)	BG105622A (ja)
BR (1)	BR9915950B1 (ja)
CA (1)	CA2353569C (ja)
CZ (1)	CZ20011960A3 (ja)
DE (1)	DE59906974D1 (ja)
EA (1)	EA200100602A1 (ja)
HU (1)	HUP0201332A3 (ja)
IL (1)	IL143449A0 (ja)
PL (1)	PL348888A1 (ja)
SK (1)	SK7472001A3 (ja)
WO (1)	WO2000034273A2 (ja)

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CN1315381C (zh) *	2003-03-13	2007-05-16	巴斯福股份公司	包含安全剂的除草混合物
CN101331119B (zh) *	2005-12-15	2012-12-12	石原产业株式会社	苯甲酰基吡唑化合物和含有它们的除草剂
WO2017113508A1 (zh) *	2015-12-31	2017-07-06	青岛清原化合物有限公司	吡唑类化合物或其盐、制备方法、除草剂组合物及用途
CN117486870A (zh) *	2023-11-03	2024-02-02	山东德浩化学有限公司	苯唑草酮衍生物及其用途

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TR199901667T2 (xx) *	1997-01-17	1999-10-21	Basf Aktiengesellschaft	3-Heterosiklil-ikame edilmi� benzoil t�revleri
HUP0204356A3 (en)	1999-12-02	2004-12-28	Basf Ag	Herbicidal cyclopropyl-anellated 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazole-derivatives, preparation and use thereof and the novel intermediates
JP2006076885A (ja) *	2002-09-13	2006-03-23	Nippon Soda Co Ltd	イミノ基を有するベンゾイル化合物及び除草剤
JP5122799B2 (ja) *	2005-12-15	2013-01-16	石原産業株式会社	ベンゾイルピラゾール系化合物及びそれらを含有する除草剤
JP5416354B2 (ja) *	2007-02-02	2014-02-12	石原産業株式会社	ベンゾイルピラゾール系化合物を含有する除草性組成物
JP6470897B2 (ja)	2012-06-29	2019-02-13	石原産業株式会社	除草効力が向上した除草組成物
CN111285863B (zh) *	2018-12-07	2022-04-26	青岛清原化合物有限公司	4-(3-杂环基-1-苯甲酰基)吡唑类化合物或其盐、制备方法、除草剂组合物及用途

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US5175299A (en)	1987-03-17	1992-12-29	Nissan Chemical Industries, Ltd.	Benzoic acid derivatives useful as intermediates for the preparation of herbicidal 4-benzoylpyrazoles
US4986845A (en)	1988-07-15	1991-01-22	Nissan Chemical Industries Ltd.	Pyrazole derivatives and herbicides containing them
TW225469B (ja)	1991-11-12	1994-06-21	Nissan Kagakl Kogyo
DE4435373A1 (de)	1994-09-22	1996-03-28	Hoechst Schering Agrevo Gmbh	Substituierte Pyrazolyl-pyrazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung
CZ293254B6 (cs)	1995-02-24	2004-03-17	Basf Aktiengesellschaft	Pyrazolylbenzoylový derivát, způsob jeho přípravy, herbicidní prostředek s jeho obsahem a způsob potírání nežádoucích rostlin
WO1997041105A1 (fr) *	1996-04-26	1997-11-06	Nippon Soda Co., Ltd.	Nouveaux derives de benzene a substitution heterocycle et herbicides
CN1076351C (zh) *	1996-04-26	2001-12-19	日本曹达株式会社	被杂环取代的苯的衍生物和除草剂
TR199901667T2 (xx) *	1997-01-17	1999-10-21	Basf Aktiengesellschaft	3-Heterosiklil-ikame edilmi� benzoil t�revleri
US6165944A (en) *	1997-01-17	2000-12-26	Basf Aktiengesellschaft	4-(3-heterocyclyl-1-benzoyl) pyrazoles and their use as herbicides
AR012142A1 (es) *	1997-03-24	2000-09-27	Dow Agrosciences Llc	Compuestos de 1-alquil-4-benzoil-5-hiroxipirazol, composiciones herbicidas que los contienen; metodo para controlar vegetacion no deseada y compuestosintermediarios utiles para preparar dichos compuestos
WO1998052926A2 (en) *	1997-05-23	1998-11-26	Dow Agrosciences Llc	1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides
DE69839310T3 (de)	1997-10-30	2015-08-06	Nippon Soda Co. Ltd.	Verwendung einer benzoylpyrazol-verbindung als herbizid.

1999
- 1999-12-02 EP EP99965430A patent/EP1135388B1/de not_active Expired - Lifetime
- 1999-12-02 IL IL14344999A patent/IL143449A0/xx unknown
- 1999-12-02 PL PL99348888A patent/PL348888A1/xx not_active Application Discontinuation
- 1999-12-02 BR BRPI9915950-3A patent/BR9915950B1/pt not_active IP Right Cessation
- 1999-12-02 SK SK747-2001A patent/SK7472001A3/sk unknown
- 1999-12-02 JP JP2000586720A patent/JP2002531562A/ja active Pending
- 1999-12-02 AU AU20949/00A patent/AU2094900A/en not_active Abandoned
- 1999-12-02 WO PCT/EP1999/009413 patent/WO2000034273A2/de not_active Application Discontinuation
- 1999-12-02 HU HU0201332A patent/HUP0201332A3/hu unknown
- 1999-12-02 AT AT99965430T patent/ATE249456T1/de not_active IP Right Cessation
- 1999-12-02 EA EA200100602A patent/EA200100602A1/ru unknown
- 1999-12-02 CA CA002353569A patent/CA2353569C/en not_active Expired - Fee Related
- 1999-12-02 US US09/857,067 patent/US6831039B1/en not_active Expired - Fee Related
- 1999-12-02 DE DE59906974T patent/DE59906974D1/de not_active Expired - Lifetime
- 1999-12-02 CZ CZ20011960A patent/CZ20011960A3/cs unknown
- 1999-12-02 KR KR1020017006942A patent/KR20010080670A/ko not_active Application Discontinuation
- 1999-12-02 CN CN99815254A patent/CN1332738A/zh active Pending
2001
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CN1315381C (zh) *	2003-03-13	2007-05-16	巴斯福股份公司	包含安全剂的除草混合物
CN101331119B (zh) *	2005-12-15	2012-12-12	石原产业株式会社	苯甲酰基吡唑化合物和含有它们的除草剂
CN102079723B (zh) *	2005-12-15	2013-04-17	石原产业株式会社	苯甲酰基吡唑化合物和含有它们的除草剂
CN102702045B (zh) *	2005-12-15	2014-05-14	石原产业株式会社	苯甲酰基吡唑化合物和含有它们的除草剂
WO2017113508A1 (zh) *	2015-12-31	2017-07-06	青岛清原化合物有限公司	吡唑类化合物或其盐、制备方法、除草剂组合物及用途
RU2707086C1 (ru) *	2015-12-31	2019-11-22	Циндао Кингагрут Кемикал Компаундз Ко., Лтд	Пиразол или его соль и способ получения, гербицидная композиция и ее применение
US11661413B2 (en)	2015-12-31	2023-05-30	Qingdao Kingagroot Chemical Compounds Co., Ltd.	Pyrazole compounds or salts thereof, preparation method therefor, herbicidal composition and use thereof
CN117486870A (zh) *	2023-11-03	2024-02-02	山东德浩化学有限公司	苯唑草酮衍生物及其用途
CN117486870B (zh) *	2023-11-03	2024-05-24	山东德浩化学有限公司	苯唑草酮衍生物及其用途

Also Published As

Publication number	Publication date
HUP0201332A2 (en)	2002-08-28
BR9915950B1 (pt)	2012-01-10
EA200100602A1 (ru)	2001-10-22
DE59906974D1 (de)	2003-10-16
HUP0201332A3 (en)	2002-12-28
IL143449A0 (en)	2002-04-21
EP1135388A2 (de)	2001-09-26
ATE249456T1 (de)	2003-09-15
JP2002531562A (ja)	2002-09-24
BG105622A (en)	2002-01-31
EP1135388B1 (de)	2003-09-10
KR20010080670A (ko)	2001-08-22
SK7472001A3 (en)	2002-01-07
CZ20011960A3 (cs)	2002-02-13
PL348888A1 (en)	2002-06-17
BR9915950A (pt)	2001-08-21
AU2094900A (en)	2000-06-26
WO2000034273A3 (de)	2000-11-02
CA2353569A1 (en)	2000-06-15
US6831039B1 (en)	2004-12-14
CA2353569C (en)	2009-07-21
WO2000034273A2 (de)	2000-06-15

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